Acetic Acid → HCID 178489316, compound

HRID 423203Notes

Reaction equation

C[O:2][C:3](OC)([CH3:32])[C:4]([C:6]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:9]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:29]=[CH:28][O:27][N:26]=3)=[CH:21][CH:20]=2)[C:8](=[O:30])[C:7]=1[OH:31])=[O:5].C(O)(=O)C>O>[O:5]=[C:4]([C:6]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:9]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:29]=[CH:28][O:27][N:26]=3)=[CH:21][CH:20]=2)[C:8](=[O:30])[C:7]=1[OH:31])[C:3](=[O:2])[CH3:32]

Participants

Conditions

Temperature: 95 °C

Procedure

4-(2,2-dimethoxypropionoyl)-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrol-2-one (0.08 g, 0.17 mmol) was added with acetic acid (0.1 mL) and water (0.9 mL). The mixture was stirred at 95° C. for 15 min. Then, water was added, the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from dichloromethane and ether to give 4-(1,2-dioxopropyl)-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrol-2-one (0.05 g, 70%) as yellow crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from dichloromethane and ether

Sources & evidence

ORD record: ord-d64ed83c6100445f85ffcb8b728834a2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101644B2

Reaction notes

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